Spectroscopic characterization of photolytically generated radical ion pairs in single-wall carbon nanotubes bearing surface-immobilized tetrathiafulvalenes

Journal of the American Chemical Society

Volumn 130, Issue 1, 2008, Pages 66-73

  Herranz, M Ángeles ^a   Ehli, Christian ^b   Campidelli, Stéphane ^c   Gutiérrez, Miriam ^a   Hug, Gordon L ^d   Ohkubo, Kei ^e   Fukuzumi, Shunichi ^e   Prato, Maurizio ^c   Martín, Nazario ^a   Guldi, Dirk M ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c UNIVERSITY OF TRIESTE   (Italy)

^d UNIVERSITY OF NOTRE DAME   (United States)

^e OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON BEAMS; ELECTRON ENERGY LEVELS; ELECTRON TRANSITIONS; PHOTOEXCITATION;

ELECTRON DONOR; ELECTRON-DONATING Π-EXTENDED TETRATHIAFULVALENE (EXTTF); VAN HOVE SINGULARITIES;

SINGLE-WALLED CARBON NANOTUBES (SWCN);

CARBON NANOTUBE; SINGLE WALLED NANOTUBE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; MATERIALS TESTING; NANOCHEMISTRY; NANOTECHNOLOGY; PHOTOCHEMISTRY; PHOTOLYSIS; SPECTROSCOPY;

ELECTRIC CONDUCTIVITY; ELECTRONS; FREE RADICALS; HETEROCYCLIC COMPOUNDS; IONS; NANOTUBES, CARBON; PHOTOLYSIS; SPECTRUM ANALYSIS; SURFACE PROPERTIES;

EID: 38349114820     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073975t     Document Type: Article

References (88)

1. (a) Fritzsche, W.; Köhler, M. Nanotechnology: An Introduction to Nanostructuring Techniques; Wiley: Weinheim, Germany, 2004.
2. (b) Rao, C. Chemistry of Nanomaterials: Synthesis, Properties and Applications; Wiley: Weinheim, Germany, 2004.
3. (c) Wolf, E. Nanophysics and Nanotechnology: An Introduction to Modern Concepts in Nanoscience; Wiley: Weinheim, Germany, 2004.
4. (d) Cao, G. Nanostructures and Nanomaterials: Synthesis, Properties & Applications; Imperial College: London, 2004.
5. (a) Carbon Nanotubes and Related Structures: New Materials for the Twenty-First Century; Harris, P., Ed.; Cambridge University Press: Cambridge, 2001.
6. (b) Sgobba, V.; Rahman, G. M. A.; Ehli, C.; Guldi, D. M. In Covalent and Non-Covalent Approaches Towards Multifunctional Carbon Nanotube Materials - Fullerenes; Langa de la Puente, F., Nierengarten, J. F., Eds.; RSC Nanoscience and Nanotechnology Series; Cambridge, United Kingdom, 2007.
7. (c) Sgobba, V.; Rahman, G. M. A.; Guldi, D. M. Carbon Nanotubes in Electron Donor-Acceptor Nanocomposites. In Chemistry of Carbon Nanotubes; Basiuk, V. A., Ed.; American Scientific Publishers: Stevenson Ranch, CA, 2006.
8. (d) Reich, S.; Thomsen, C.; Maultzsch, J. Carbon Nanotubes: Basic Concepts and Physical Properties; VCH: Weinheim, Germany, 2004.
9. (e) Acc. Chem. Res. 2002, 35 (Special Issue), 997-1113.
10. (a) Carbon Nanotubes: Synthesis, Structure, Properties and Applications; Dresselhaus, M. S., Dresselhaus, G., Avouris P., Eds.; Springer: Berlin, 2001.
11. (b) Reich, S.; Thomsen, C.; Maultzsch, J. Carbon Nanotubes: Basic-Concepts and Physical Properties; Wiley-VCH: Weinheim, Germany, 2004.
12. (c) Popov, V. N.; Lambin, P. Carbon Nanotubes; Springer: Dordrecht, The Netherlands, 2006.
13. (d) Interface 2006, 15 (Special Issue), 23-65.
14. For reviews, see: (a) Hirsch, A. Angew. Chem., Int. Ed. 2002, 41, 1853-1859.
15. (b) Barh, J. L.; Tour, J. M. J. Mater. Chem. 2002, 12, 1952-1958.
16. (c) Nigoyi, S.; Hamon, M. A.; Hu, H.; Zhao, B.; Bhomwik, P.; Sen, R.; Itkis, M. E.; Haddon, R. C. Acc. Chem. Res. 2002, 35, 1105-1013.
17. (d) Sun, Y.-P.; Fu, K.; Lin, Y.; Huang, W. Acc. Chem. Res. 2002, 35, 1096-1104.
18. (e) Banerjee, S.; Kahn, M. G. C.; Wong, S. S. Chem. Eur. J. 2003, 9, 1898-1908.
19. (f) Tasis, D.; Tagmatarchis, N.; Georgakilas, V.; Prato, M. Chem. Eur. J. 2003, 9, 4001-4008.
20. (g) Dyke, C. A.; Tour, J. M. Chem. Eur. J. 2004, 10, 812-817.
21. (h) Banerjee, S.; Hemraj-Benny, T.; Wong, S. S. Adv. Mater. 2005, 17, 17-29.
22. (i) Guldi, D. M.; Rahman, G. M. A.; Zerbetto, F.; Prato, M. Acc. Chem. Res. 2005, 38, 871-878.
23. (j) Tasis, D.; Tagmatarchis, N.; Bianco, A. Chem. Rev. 2006, 106, 1105-1136.
24. (k) Guldi, D. M.; Rahman, G. M. A.; Sgobba, V.; Ehli, C. Chem. Soc. Rev. 2006, 35, 471-487.
25. (l) Guldi, D. M. Phys. Chem. Chem. Phys. 2007, 1400-1420.
26. (a) Tans, S. J.; Devoret, M. H.; Dai, H.; Thess, A.; Smalley, R. E.; Geerligs, L. J.; Dekker, C. Nature 1997, 386, 474-477.
27. (b) Tans, S. J.; Verschnesen, A. R. M.; Dekker, C. Nature, 1998, 393, 49-52.
28. (c) Paulson, S.; Helsen, A.; Buongiorno, N. M.; Taylor, R. M.; Falvo, M.; Superfine, R.; Washburn, S. Science 2000, 290, 1942-1949.
29. (d) O'Connel, M. J.; Bachilo, S. M.; Huffmann, C. B.; Moore, V. C.; Strano, M. S.; Haroz, E. H.; Rialon, K. L.; Boul, P. J.; Noon, W. H.; Kittrell, C.; Hauge, J. M. R. H.; Weisman, R. B.; Smalley, R. E. Science, 2002, 297, 593-596.
30. (e) Dalton, A. B.; Collins, S.; Muñoz, E.; Razal, J. M.; Ebron, V. H.; Ferraris, J. P.; Coleman, J. N.; Kim, B. G.; Baughman, R. H. Nature 2003, 423, 703-703.
31. (f) Javey, A.; Guo, J.; Wang, Q.; Lundstrom, M.; Dai, H. J. Nature 2003, 423, 654-657.
32. (a) Heller, I.; Kong, J.; Williams, K. A.; Dekker, C.; Lemay, S. G. J. Am. Chem. Soc. 2006, 128, 7353-7359.
33. (b) Heller, I.; Kong, J.; Heering, H. A.; Williams, K. A.; Lemay, S. G.; Dekker, C. Nano Lett. 2005, 5, 137-142.
34. (c) Day, T. M.; Wilson, N. R.; Macpherson, J. V. J. Am. Chem. Soc. 2004, 126, 16724-16725.
35. (d) Ehli, C.; Rahman, G. M. A.; Jux, N.; Balbinot, D.; Guldi, D. M.; Paolucci, F.; Marcaccio, M.; Paolucci, D.; Melle-Franco, M.; Zerbetto, F.; Campidelli, S.; Prato, M. J. Am. Chem. Soc. 2006, 128, 11222-11231.
36. (a) Guldi, D. M.; Marcaccio, M.; Paolucci, D.; Paolucci, F.; Tagmatarchis, N.; Tasis, D.; Vázquez, E.; Prato, M. Angew. Chem., Int. Ed. 2003, 42, 4206-4209.
37. (b) Li, H.; Martin, R. B.; Harruff, B. A.; Carino, R. A.; Allard, L. F.; Sun, Y.-P. Adv. Mater. 2004, 16, 896-900.
38. (c) Guldi, D. M.; Rahman, G. M. A.; Ramey, J.; Marcaccio, M.; Paolucci, D.; Paolucci, F.; Qin, S.; Ford, W. T.; Balbinot, D.; Jux, N.; Tagmatarchis, N.; Prato, M. Chem. Commun. 2004, 2034-2035.
39. (d) Guldi, D. M.; Taieb, H.; Rahman, G. M. A.; Tagmatarchis, N.; Prato, M. Adv. Mater. 2005, 17, 871-875.
40. (e) Guldi, D. M.; Rahman, G. M. A.; Prato, M.; Jux, N.; Qin, S.; Ford, W. Angew. Chem., Int. Ed. 2005, 44, 2015-2018.
41. (f) Baskaran, D.; Mays, J. W.; Zhang, X. P.; Bratcher, M. S. J. Am. Chem. Soc. 2005, 127, 6916-6917.
42. (g) Rahman, G. M. A.; Guldi, D. M.; Cagnoli, R.; Mucci, A.; Schenetti, L.; Vaccari, L.; Prato, M. J. Am. Chem. Soc. 2005, 127, 10051-10057.
43. (h) Guldi, D. M.; Rahman, G. M. A.; Qin, S.; Tchoul, M.; Ford, W. T.; Marcaccio, M.; Paolucci, D.; Paolucci, F.; Campidelli, S.; Prato, M. Chem. Eur. J. 2006, 12, 2152-2161.
44. (i) Alvaro, M.; Atienzar, P.; de la Cruz, P.; Delgado, J. L.; Troiani, V.; García, H.; Langa, F.; Palkar, A.; Echegoyen, L. J. Am. Chem. Soc. 2006, 128, 6626-6635.
45. (j) Campidelli, S.; Sooambar, C.; Lozano-Diz, E.; Ehli, C.; Guldi, D. M.; Prato, M. J. Am. Chem. Soc. 2006, 128, 12544-12552.
46. (a) Hecht, D. S.; Ramirez, R. J. A.; Briman, M.; Artukovic, E.; Chichak, K. S.; Stoddart, J. F.; Gruner, G. Nano Lett. 2006, 6, 2031-2036.
47. (b) Rao, A. M.; Eklund, P. C.; Bandow, S.; Thess, A.; Smalley, R. E. Nature 1997, 388, 257-259.
48. (a) Herranz, M. A.; Martín, N.; Campidelli, S.; Prato, M.; Brehm, G.; Guldi, D. M. Angew. Chem., Int. Ed. 2006, 45, 4478-4482.
49. (b) Guldi, D. M.; Rahman, G. M. A.; Rahman Sgobba, V.; Bonifazi, D.; Prato, M.; Kotov, N. A. J. Am. Chem. Soc. 2006, 128, 2315-2323.
50. (c) Melle-Franco, M.; Marcaccio, M.; Paolucci, F.; Georgakilas, V.; Guldi, D. M.; Prato, M.; Zerbetto, F. J. Am. Chem. Soc. 2004, 126, 1646-1647.
51. X-ray photoemission spectroscopy (XPS) and near-edge X-ray-absorption fine structure (NEXAFS) spectroscopy signatures of carrier-doped SWNT have been investigated. See: Shiraishi, M.; Swaraj, S.; Takenobu, T.; Iwasa, Y.; Ata, M.; Unger, W. E. S. Phys. Rev. B 2005, 71, 125419.
52. (a) See, for example: Holzinger, M.; Hirsch, A.; Bernier, P.; Duesberg, G. S.; Burghard, M. Appl. Phys. A 2000, 70, 599-602.
53. (b) Georgakilas, V.; Kordatos, K.; Prato, M.; Guldi, D. M.; Holzinger, M.; Hirsch, A. J. Am. Chem. Soc. 2002, 124, 760.
54. (a) Strano, M. S.; Dyke, C. A.; Usrey, M. L.; Barone, P. W.; Allen, M. J.; Shan, H.; Kittrell, C.; Hauge, R. H.; Tour, J. M.; Smalley, R. E. Science 2003, 301, 1519-1522.
55. (b) Zurek, E.; Autschbach, J. J. Am. Chem. Soc. 2004, 126, 13079-13088.
56. (a) Star, A.; Stoddart, J. F.; Steuerman, D.; Diehl, M.; Boukai, A.; Wong, E. W.; Yang, X.; Chung, S. W.; Choi, H.; Heath, J. R. Angew. Chem., Int. Ed. 2001, 40, 1721-1725.
57. (b) Chen, J.; Liu, H. Y.; Weimer, W. A.; Halls, M. D.; Waldeck, D. H.; Walker, G. C. J. Am. Chem. Soc. 2002, 124, 9034-9035.
58. (c) Gomez, F. J.; Chen, R. J.; Wang, D. W.; Waymouth, R. M.; Dai, H. J. Chem. Commun. 2003, 190-191.
59. Chen, R. J.; Zhang, Y.; Wang, D.; Dai, H. J. Am. Chem. Soc. 2001, 123, 3838-3839.
60. Nakashima, N.; Tomonari, Y.; Murakami, H. Chem. Lett. 2002, 638-639.
61. (a) Petrov, P.; Stassin, F.; Pagnoulle, C.; Jerome, R. Chem. Commun. 2003, 2904-2905.
62. (b) Liu, L.; Wang, T. X.; Li, J. X.; Guo, Z. X.; Dai, L. M.; Zhang, D. Q.; Zhu, D. B. Chem. Phys. Lett. 2003, 367, 747-752.
63. Zhang, J.; Lee, J. K.; Wu, Y.; Murray, R. W. Nano Lett. 2003, 3, 403-407.
64. For recent examples, see: (a) Guldi, D. M.; Rahman, G. M. A.; Jux, N.; Balbinot, D.; Hartnagel, U.; Tagmatarchis, N.; Prato, M. J. Am. Chem. Soc. 2005, 127, 9830-9838.
65. (b) Hasobe, T.; Fukuzumi, S.; Kamat, P. V. J. Am. Chem. Soc. 2005, 127, 11884-11885.
66. (c) Satake, A.; Miyajima, Y.; Kobuke, Y. Chem. Mater. 2005, 17, 716-724.
67. (d) Sgobba, V.; Rahman, G. M. A.; Guldi, D. M.; Jux, N.; Campidelli, S.; Prato, M. Adv. Mater. 2006, 18, 2264-2269.
68. Li, H.; Zhou, B.; Lin, Y.; Gu, L.; Wang, W.; Fernando, K. A. S.; Kumar, S.; Allard, L. F.; Sun, Y.-P. J. Am. Chem. Soc. 2004, 126, 1014-1015.
69. 60-exTTF conjugates, see: (a) Martín, N.; Sánchez, L.; Guldi, D. M. Chem. Commun. 2000, 113-114.
70. (b) Herranz, M. A.; Martín, N.; Ramey, J.; Guldi, D. M. Chem. Commun. 2002, 2968-2969.
71. (c) Sánchez, L.; Pérez, I.; Martín, N.; Guldi, D. M. Chem. Eur. J. 2003, 9, 2457-2468.
72. (d) Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 5340-5341.
73. (e) Giacalone, F.; Martín, N.; Ramey, J.; Guldi, D. M. Chem. Eur. J. 2005, 11, 4819-4834.
74. (f) Handa, S.; Giacalone, F.; Haque, S. A.; Palomares, E.; Martín, N.; Durrant, J. R. Chem. Eur. J. 2005, 11, 7440-7447.
75. (g) Sánchez, L.; Sierra, M.; Martín, N.; Guldi, D. M.; Wienk, M. W.; Janssen, R. A. J. Org. Lett. 2005, 128, 1048-10490.
76. (h) Martín, N. Chem. Commun. 2006, 2093-2104.
77. (i) Atienza, C.; Martín, N.; Wielopolski, M.; Haworth, N.; Clark, T.; Guldi, D. M. Chem. Commun. 2006, 3202-3204.
78. González, S.; Martín, N.; Guldi, D. M. J. Org. Chem. 2003, 68, 779-791.
79. Pyrene-exTTF) ≈ 750. The low ratio is likely due to the solubility of pyrene-exTTF in THF. Obviously, we formulate a competition between the SWNT immobilization and the complete solubilization by the solvent. The mechanism is quite different from the case noted for amphiphilic pyrene derivatives that we used in previous work, where a ratio of 1 to 280 carbon atoms was extrapolated (ref 6d): Amphiphilic pyrene derivatives form aggregates in water and in the presence of SWNT; the association of the apolar moiety with the SWNT sidewall results in a gain of energy leading to a stable suspension.
80. Marcolongo, G.; Ruaro, G.; Gobbo, M.; Meneghetti, M. Chem. Commun, 2007, 4925-4927.
81. Herranz, M. A.; Yu, L.; Echegoyen, L.; Martín, N. J. Org. Chem. 2003, 68, 8379-8385.
82. Guldi, D. M.; Menna, E.; Maggini, M.; Marcaccio, M.; Paolucci, D.; Paolucci, F.; Campidelli, S.; Prato, M.; Rahman, G. M. A.; Schergna, S. Chem. Eur. J. 2006, 12 3975-3983.
83. In time-resolved fluorescence measurements the only detectable component reveals a lifetime of around 16 ns.
84. Saito, K.; Troiani, V.; Qiu, H.; Solladie, N.; Sakata, T.; Mori, H.; Ohama, M.; Fukuzumi, S. J. Phys. Chem. C 2007, 111, 1194-1199.
85. (a) Barone, V.; Peralta, J. E.; Wert, M.; Heyd, J.; Scuseria, G. E. Nano Lett. 2005, 5, 1621-1624.
86. (b) Spataru, C. D.; Ismael-Beigi, S.; Benedict, L. X.; Louie, S. G. Phys. Rev. Lett. 2004, 92, 077402(1)- 077402(4).
87. (c) Zhou, Z.; Steigerwald, M.; Hybertsen, M.; Brus, L.; Friesner, R. A. J. Am. Chem. Soc. 2004, 126, 3597-3607.
88. The spectrum of the reduced state was determined by simply subtracting the changes - seen in the differential absorption spectrum - from the ground state.